Consumers use headphones for enjoying music, audio books, podcasts, or other types of media in a variety of different situations throughout the day. During routine daily wear, headphone qualities such as comfort and flexibility may be desired. However, for sports activity, users require a stable and secure fit that can withstand more vigorous movement. Neckband or collar-style headphones are often selected by consumers to function for these various uses, where these types of headphones include an around-the-neck band structure with left and right side earphones attached to the band. Existing neckband headphones may feature a fixed-curvature, one-size-fits-all band design sized to fit loosely around the neck to provide all-day comfort, but which does not fit securely enough for sports. Other existing neckband headphones may be designed with a fixed-curvature band having a tighter radius for an athletic fit that provides stability during sports, but that is uncomfortable for long wearing periods.